Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/02—Polycondensates containing more than one epoxy group per molecule
  • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
• • G—PHYSICS
  • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
  • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
  • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
• • G—PHYSICS
  • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
  • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
  • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
  • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
  • H05B33/00—Electroluminescent light sources
  • H05B33/02—Details
  • H05B33/04—Sealing arrangements, e.g. against humidity
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
  • H05B33/00—Electroluminescent light sources
  • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/10—Encapsulations, e.g. protective coatings characterised by their shape or disposition
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
  • H10K59/80—Constructional details
  • H10K59/87—Passivation; Containers; Encapsulations
  • H10K59/871—Self-supporting sealing arrangements
  • H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
  • H10K59/80—Constructional details
  • H10K59/87—Passivation; Containers; Encapsulations
  • H10K59/873—Encapsulations

Definitions

• the present invention relates to a composition.
• organic optical devices using organic thin film devices such as organic electroluminescence (organic EL) display devices has been promoted.
• organic EL organic electroluminescence
• Photocurable sealants are known as (for example, Patent Documents 1 to 5).
• Japanese Unexamined Patent Publication No. 2001-357973 Japanese Patent No. 5919574 Japanese Patent No. 4800247 Japanese Unexamined Patent Publication No. 2016-058273 Japanese Patent No. 4384509
• One aspect of the present invention contains a cationically polymerizable compound having a cationic ring-opening polymerizable group, a vinyl ether-based compound having a vinyloxy group, and a photocationic polymerization initiator, and the content of the vinyl ether-based compound is high.
• the present invention relates to a composition which is larger than 50 parts by mass and 95 parts by mass or less with respect to 100 parts by mass of the total of the cationically polymerizable compound and the vinyl ether compound.
• the above composition is a combination of a vinyl ether compound having a vinyl oxy group and a cationically polymerizable compound, and the content of the vinyl ether compound is a certain amount or more.
• the composition can achieve both low viscosity and excellent moisture resistance and transparency after curing. From this, the organic electroluminescence display sealing agent containing the above composition can be easily applied uniformly to the members and is excellent in workability. Further, since the composition is excellent in moisture resistance and transparency after curing, an organic electroluminescence display device having excellent reliability can be realized by using the composition as a sealing agent for displaying organic electroluminescence.
• the viscosity of the vinyl ether compound at 25 ° C. may be lower than the viscosity of the cationically polymerizable compound at 25 ° C.
• the cationic ring-opening polymerizable group may be selected from the group consisting of an epoxy group and an oxetane group.
• the content of the photocationic polymerization initiator may be 0.1 parts by mass or more and 5.0 parts by mass or less with respect to 100 parts by mass in total of the cationically polymerizable compound and the vinyl ether compound.
• composition according to one embodiment may further contain a curing retarder.
• the viscosity when measured using an E-type viscometer under the conditions of 25 ° C. and 10 rpm may be 2 to 200 cps.
• the vinyl ether compound may have two vinyl oxy groups and further have a cyclic group.
• Another aspect of the present invention relates to a sealing agent for an organic electroluminescence display element containing the above-mentioned composition.
• Yet another aspect of the present invention relates to a cured product of the above-mentioned sealant for an organic electroluminescence display element.
• the total light transmittance at a wavelength of 380 to 800 nm per 10 ⁇ m thickness may be 80% or more.
• Yet another aspect of the present invention relates to a sealing material for an organic electroluminescence display element, which contains the above-mentioned cured product.
• Yet another aspect of the present invention relates to an organic electroluminescence display device including the organic electroluminescence display device and the above-mentioned sealing material for the organic electroluminescence display device.
• Still another aspect of the present invention is a bonding step of attaching the above-mentioned sealing agent for an organic electroluminescence display element to the first member, and light is applied to the above-mentioned sealing agent for an organic electroluminescence display element.
• An organic electroluminescence display comprising an irradiation step of irradiating and a bonding step of bonding the first member and the second member via the light-irradiated sealant for the organic electroluminescence display element.
• a composition having a low viscosity and excellent reliability after curing there is provided a composition having a low viscosity and excellent reliability after curing. Further, according to the present invention, a sealing agent for an organic EL display element containing the above composition, a cured product of the sealing agent for the organic EL display element, a sealing material containing the cured body, and the sealing material are included. An organic EL display device and a method for manufacturing the organic EL display device are provided.
• the composition according to this embodiment can be used as a resin composition.
• the resin composition according to the present embodiment contains a cationically polymerizable compound (component (A)), a vinyl ether compound (component (B)), and a photocationic polymerization initiator (component (C)).
• the cationically polymerizable compound (component (A)) has a cationic ring-opening polymerizable group.
• the vinyl ether compound (component (B)) has a vinyl oxy group.
• the content of the vinyl ether compound is more than 50 parts by mass and 95 parts by mass or less with respect to 100 parts by mass in total of the cationically polymerizable compound and the vinyl ether compound.
• the resin composition according to the present embodiment is a combination of a vinyl ether compound having a vinyl oxy group and a cationically polymerizable compound, and the content of the vinyl ether compound is a certain amount or more.
• the resin composition can achieve both low viscosity and excellent moisture resistance and transparency after curing. Therefore, the encapsulant for an organic electroluminescence (EL) display device (hereinafter, also simply referred to as a encapsulant) containing the resin composition according to the present embodiment can form a highly reliable encapsulant and is reliable. An organic EL display device having excellent properties can be realized.
• EL organic electroluminescence
• Component (A) cationically polymerizable compound
• the component (A) is a compound having a cationic ring-opening polymerizable property, and can also be said to be a compound having a cationic ring-opening polymerizable group.
• the cationic ring-opening polymerizable group include a cyclic ether group (for example, an epoxy group (oxylan ring)) and an oxetane group (oxetane ring), which are composed of an epoxy group and an oxetane group from the viewpoint of adhesiveness and moisture resistance. At least one selected from the group is preferred.
• the component (A) may be a compound having one cationic ring-opening polymerizable group, or may be a compound having two or more.
• the component (A) preferably has two or more cationic ring-opening polymerizable groups, and more preferably two cationic ring-opening polymerizable groups.
• Examples of the compound having an epoxy group include a compound having an epoxy group and an alicyclic group (hereinafter, also referred to as an alicyclic epoxy compound) and a compound having an epoxy group and an aromatic group (hereinafter, may be referred to as an alicyclic epoxy compound) from the viewpoint of adhesiveness and moisture resistance.
• an alicyclic epoxy compound a compound having an epoxy group and an aromatic group
• at least one selected from the group consisting of aromatic epoxy compounds is preferable.
• the component (A1) may be a compound having one epoxy group or a compound having two or more epoxy groups.
• the component (A1) preferably has two or more epoxy groups, and more preferably has two epoxy groups.
• the component (A1) may be a compound having no aromatic ring.
• the component (A1) may be used alone or in combination of two or more.
• the component (A1) may be, for example, a compound obtained by epoxidizing a compound having a cycloalkene ring or a derivative thereof.
• the cycloalkene ring include a cyclohexene ring, a cyclopentene ring, a pinene ring and the like.
• Epoxylation can be carried out using, for example, an oxidizing agent.
• the oxidizing agent include hydrogen peroxide and peracid.
• Examples of such (A1) components include 3', 4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate and 3,4-epoxycyclohexylalkyl (meth) acrylate (eg, 3,4-epoxy). Cyclohexylmethyl (meth) acrylate and the like), (3,3', 4,4'-diepoxy) bicyclohexyl and the like.
• the component (A1) may be, for example, a compound obtained by hydrogenating a compound having an epoxy group and an aromatic ring, or a derivative thereof.
• the compound having an epoxy group and an aromatic ring include bisphenol A type epoxy resin and bisphenol F type epoxy resin.
• Examples of such (A1) component include hydrogenated bisphenol A type epoxy resin, hydrogenated bisphenol F type epoxy resin and the like.
• a compound having a 1,2-epoxycyclohexane structure is preferable.
• Examples of the compound having a 1,2-epoxycyclohexane structure include a compound represented by the formula (A1-1).
• X represents a single bond or a linking group (a divalent group having one or more atoms).
• the compound represented by the formula (A1-1) is (3,3', 4,4'-diepoxy) bicyclohexyl.
• X is preferably a linking group.
• the linking group may be, for example, a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide bond, or a group in which a plurality of these are linked.
• a group having an ester bond is preferable, and a group in which an ester bond and a divalent hydrocarbon group are linked is more preferable.
• an alkanediyl group is preferable, and an alkanediyl group having 1 to 3 carbon atoms is more preferable.
• the molecular weight of the component (A1) is preferably 450 or less, more preferably 400 or less, further preferably less than 300, still more preferably 280 or less, from the viewpoint of storage stability of the resin composition and moisture resistance of the cured product.
• the molecular weight of the component (A1) may be, for example, 100 or more.
• the number average molecular weight of the component (A1) is preferably in the above range.
• the number average molecular weight indicates a polystyrene-equivalent value measured by gel permeation chromatography (GPC) under the following measurement conditions.
• the aromatic epoxy compound may be a compound having one epoxy group or a compound having two or more epoxy groups.
• the aromatic epoxy compound preferably has two or more epoxy groups, and more preferably has two epoxy groups.
• the aromatic epoxy compound may be a compound having no alicyclic group.
• the aromatic epoxy compound may be used alone or in combination of two or more.
• component (A2) examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, biphenyl type epoxy resin, naphthalene type epoxy resin, fluorene type epoxy resin, novolac phenol type epoxy resin, and cresol novolac.
• component (A2) examples include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, biphenyl type epoxy resin, naphthalene type epoxy resin, fluorene type epoxy resin, novolac phenol type epoxy resin, and cresol novolac.
• Examples include type epoxy resins and modified products thereof.
• a compound having a bisphenol structure for example, bisphenol A structure, bisphenol F structure, bisphenol S structure, etc.
• One type is more preferable.
• Examples of the component (A2) include a compound represented by the formula (A2-1).
• n represents a real number of 0.1 to 30, and R 21 , R 22 , R 23 and R 24 are carbons that may independently have a hydrogen atom or a substituent. It shows an alkyl group of the number 1-5. When there are a plurality of R 23s and R 24s , they may be the same or different from each other.
• Examples of the substituent that the alkyl group may have include a fluorine atom and an oxyalkyl group, and among these, a fluorine atom is preferable.
• R 21 , R 22 , R 23 and R 24 are preferably hydrogen atoms or methyl groups. Further, it is preferable that R 21 , R 22 , R 23 and R 24 are all the same group.
• the molecular weight of the component (A2) is preferably 100 or more, more preferably 150 or more, still more preferably 200 or more, from the viewpoint of moisture resistance of the cured product.
• the molecular weight of the component (A2) is preferably 5000 or less, more preferably 1000 or less, and most preferably 450 or less from the viewpoint of moisture resistance of the cured product.
• the number average molecular weight of the component (A2) is in the above range.
• the number average molecular weight indicates a polystyrene-equivalent value measured by gel permeation chromatography (GPC) under the above-mentioned measurement conditions.
• Examples of the compound having an oxetane group include the following (A3) component.
• the component (A3) may be a compound having one oxetane group, or may be a compound having two or more oxetane groups.
• the component (A3) may be used alone or in combination of two or more.
• component (A3) examples include 3-ethyl-3-hydroxymethyloxetane (manufactured by Toa Synthetic Co., Ltd., trade name OXT-101, etc.), 1,4-bis [(3-ethyl-3-oxetanyl) methoxy).
• Methyl] benzene (manufactured by Toa Synthetic Co., Ltd., trade name OXT-121, etc.), 3-ethyl-3- (phenoxymethyl) oxetane (manufactured by Toa Synthetic Co., Ltd., trade name OXT-211, etc.), di (1- Ethyl- (3-oxetanyl)) methyl ether (manufactured by Toa Synthetic Co., Ltd., trade name OXT-221 etc.), 3-Ethyl-3- (2-ethylhexyloxymethyl) oxetane (manufactured by Toa Synthetic Co., Ltd., product) Name OXT-212 etc.) and the like.
• the component (A) may be a compound other than the component (A1), the component (A2) and the component (A3). Examples of such a compound include the following component (A4).
• the component (A4) may be a compound having a cationic ring-opening polymerizable group, and may be, for example, a compound having a cyclic ether group.
• the component (A4) may be a compound having one cationic ring-opening polymerizable group, and preferably has two or more.
• the component (A4) may be a compound having no alicyclic group, aromatic ring and oxetane group.
• the component (A4) may be used alone or in combination of two or more.
• examples of the compound having a cyclic ether group include compounds having an epoxy group (oxylan ring).
• a compound having a glycidyloxy group is preferable.
• the compound having a glycidyloxy group is preferably a compound having two or more glycidyloxy groups.
• Examples of the compound having a glycidyloxy group include diglycidyl ether of alkylene glycol, diglycidyl ether of polyalkylene glycol, di or triglycidyl ether of glycerin or its alkylene oxide adduct.
• Examples of the alkylene glycol include ethylene glycol, propylene glycol, 1,6-hexanediol and the like.
• Examples of the polyalkylene glycol include polyethylene glycol or an alkylene oxide adduct thereof, polypropylene glycol or an alkylene oxide adduct thereof.
• Examples of the alkylene oxide include ethylene oxide and propylene oxide.
• the content of the component (A) may be, for example, 5 parts by mass or more out of a total of 100 parts by mass of the components (A) and (B), and 10 parts by mass from the viewpoint of further improving the durability after curing. It is preferably 20 parts by mass or more, and more preferably 20 parts by mass or more. Further, the content of the component (A) may be, for example, 49.9 parts by mass or less in a total of 100 parts by mass of the components (A) and (B), from the viewpoint of further improving the durability after curing. Is preferably 40 parts by mass or less, and more preferably 30 parts by mass or less.
• the component (B) is a compound having a vinyloxy group.
• the component (B) one type can be used alone or two or more types can be used in combination.
• examples of such compounds include ethylene glycol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, propylene glycol divinyl ether, dipropylene glycol divinyl ether, butanediol divinyl ether, hexanediol divinyl ether, and cyclohexanedimethanol divinyl ether.
• Di or trivinyl ether compounds such as trimethylpropan trivinyl ether, ethyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, octadecyl vinyl ether, cyclohexyl vinyl ether, hydroxybutyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexanedimethanol monovinyl ether, n-propyl vinyl ether.
• trivinyl ether compounds such as trimethylpropan trivinyl ether, ethyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, octadecyl vinyl ether, cyclohexyl vinyl ether, hydroxybutyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexanedimethanol monovinyl ether, n-propyl vinyl ether.
• the component (B) preferably has two vinyloxy groups and further has a cyclic group.
• Examples of such component (B) include cyclohexanedimethanol divinyl ether, 2,2-adamantane dimethanol divinyl ether and the like.
• the content of the component (B) is preferably larger than 50 parts by mass, more preferably 51 parts by mass or more, based on 100 parts by mass of the total of the components (A) and (B). , 60 parts by mass or more is more preferable, and 70 parts by mass or more is further preferable. Further, the content of the component (B) is preferably 95 parts by mass or less with respect to 100 parts by mass in total of the components (A) and (B) from the viewpoint that a cured product having excellent durability can be easily obtained. It is more preferably 85 parts by mass or less, and further preferably 75 parts by mass or less.
• the viscosity (initial viscosity) of the component (B) at 25 ° C. is not particularly limited, but is preferably lower than the viscosity of the component (A) at 25 ° C. from the viewpoint of keeping the viscosity low.
• the component (C) may be any component that can be activated by light to initiate cationic polymerization of the component (A).
• the component (C) one type can be used alone or two or more types can be used in combination.
• component (C) examples include aryl sulfonium salt derivatives (for example, Cyracure UVI-6990 and Cyracure UVI-6974 manufactured by Dow Chemical Co., Ltd., Adekaoptomer SP-150 manufactured by Asahi Denka Kogyo Co., Ltd., and Adekaoptomer SP-152.
• aryl sulfonium salt derivatives for example, Cyracure UVI-6990 and Cyracure UVI-6974 manufactured by Dow Chemical Co., Ltd., Adekaoptomer SP-150 manufactured by Asahi Denka Kogyo Co., Ltd., and Adekaoptomer SP-152.
• Adekaoptomer SP-170 Adekaoptomer SP-172, CPI-100P, CPI-101A, CPI-200K, CPI-210S, LW-S1, Double Bond CibaCure-1190, etc.
• Aryliodonium salt derivatives for example, Irgacure 250 manufactured by Tivas Specialty Chemicals, RP-2074 manufactured by Rhodia Japan, etc.
• allen-ion complex derivatives for example, Irgacure 250 manufactured by Tivas Specialty Chemicals, RP-2074 manufactured by Rhodia Japan, etc.
• allen-ion complex derivatives for example, Irgacure 250 manufactured by Tivas Specialty Chemicals, RP-2074 manufactured by Rhodia Japan, etc.
• allen-ion complex derivatives for example, Irgacure 250 manufactured by Tivas Specialty Chemicals, RP-2074 manufactured by Rhodia Japan, etc.
• allen-ion complex derivatives for example, Irgacure 250 manufactured by Tivas Specialty Chemicals
• an onium salt compound is preferable from the viewpoint of obtaining the above-mentioned effects more remarkably.
• Examples of the onium salt compound of the component (C) include an onium salt compound represented by the formula (C-1).
• A represents an element having a valence m of the genus VIA to VIIA, and m represents 1 or 2.
• p represents an integer of 0 to 3.
• R represents an organic group attached to A.
• X - represents the counterion of onium, the number of which is (p + 1) per molecule.
• D represents a divalent group represented by the following formula (C-1-1).
• the plurality of Rs may be the same or different from each other.
• a plurality of X -s may be the same as or different from each other. When there are multiple A's, they may be the same or different from each other. When there are multiple D's, they may be the same or different from each other.
• E represents a divalent group
• G is -O-, -S-, -SO-, -SO 2- , -NH-, -NR'-, -CO-. , -COO-, -CONH-, an alkylene group having 1 to 3 carbon atoms, or a phenylene group (R'is an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 10 carbon atoms).
• a indicates an integer from 0 to 5.
• the a + 1 E and the a G may be the same or different from each other.
• R is an organic group bonded to A, which is an aryl group having 6 to 30 carbon atoms, a heterocyclic group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, and the like.
• it represents an alkynyl group having 2 to 30 carbon atoms, which are an alkyl group, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, or an arylthio group.
• the number of Rs is (m + p (m-1) + 1), and a plurality of Rs may be the same or different from each other.
• two or more R are directly or, -O -, - S -, - SO -, - SO 2 -, - NH -, - NR '-, - CO -, - COO -, - CONH- , It may be bonded via an alkylene or phenylene group having 1 to 3 carbon atoms to form a ring structure containing the element A.
• R' represents an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 10 carbon atoms.
• aryl group having 6 to 30 carbon atoms examples include a monocyclic aryl group such as a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a benzanthrasenyl group and an anthraquinolyl group.
• a fused polycyclic aryl group such as a fluorenyl group, a naphthoquinone group and an anthraquinone group.
• An aryl group having 6 to 30 carbon atoms, a heterocyclic group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms is one or more. It may have a substituent.
• Linear alkyl groups with 1 to 18 carbon atoms such as methyl group, ethyl group, propyl group, butyl group, pentyl group, octyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group and octadecyl group;
• Branched alkyl groups having 1 to 18 carbon atoms such as isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, tert-pentyl group and isohexyl group; Cycloalkyl group having 3 to 18 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Hydroxy group; Linear group with 1 to 18 carbon atoms such as methoxy group,
• Branched alkoxy group Acetyl group, propionyl group, butanoyl group, 2-methylpropionyl group, heptanoil group, 2-methylbutanoyl group, 3-methylbutanoyl group, octanoyl group, decanoyl group, dodecanoyl group, octadecanoyl group, etc.
• Arylcarbonyl groups having 7 to 11 carbon atoms such as benzoyl groups and naphthoyl groups; Methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, isobutoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, octyloxycarbonyl group, tetradecyloxycarbonyl group, octa
• a linear or branched alkoxycarbonyl group having 2 to 19 carbon atoms such as a decyloxycarbonyl group
• Aryloxycarbonyl groups having 7 to 11 carbon atoms such as phenoxycarbonyl groups and naphthoxycarbonyl groups
• An arylthiocarbonyl group having 7 to 11 carbon atoms such as a phenylthiocarbonyl group and a naphthoxythio
• a linear or branched alkylthio group having 1 to 18 carbon atoms such as a decylthio group and a dodecylthio group;
• Aryl groups having 6 to 10 carbon atoms such as phenyl group, tolyl group, dimethylphenyl group and naphthyl group; Thienyl group, furanyl group, pyranyl group, pyrrolyl group, oxazolyl group, thiazolyl group, pyridyl group, pyrimidyl group, pyrazinyl group, indolyl group, benzofuranyl group, benzothienyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, carbazolyl Number of carbon atoms of group, acridinyl group, phenothiazinyl group, phenazinyl group, xanthenyl group, thianthrenyl group,
• Aryloxy groups having 6 to 10 carbon atoms such as phenoxy groups and naphthyloxy groups; Methylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, butylsulfinyl group, isobutylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, pentylsulfinyl group, isopentylsulfinyl group, neopentylsulfinyl group, A linear or branched alkylsulfinyl group having 1 to 18 carbon atoms such as a tert-pentylsulfinyl group and an octylsulfinyl group; Arylsulfinyl groups having 6 to 10 carbon atoms such as phenoxy groups and naphth
• Q represents a hydrogen atom or a methyl group
• k represents an integer of 1 to 5.
• the k Qs may be the same or different from each other.
• onium ion (A + ) in the formula (C-1) a sulfonium ion, an iodonium ion, and a selenium ion are preferable. Representative examples of these are shown below.
• sulfonium ion examples include triphenylsulfonium, tri-p-tolylsulfonium, tri-o-tolylsulfonium, tris (4-methoxyphenyl) sulfonium, 1-naphthyldiphenylsulfonium, 2-naphthyldiphenylsulfonium, and tris (4-).
• Fluorophenyl) sulfonium tri-1-naphthylsulfonium, tri-2-naphthylsulfonium, tris (4-hydroxyphenyl) sulfonium, 4- (phenylthio) phenyldiphenylsulfonium, 4- (p-tolylthio) phenyldi-p-tolylsulfonium , 4- (4-methoxyphenylthio) phenylbis (4-methoxyphenyl) sulfonium, 4- (phenylthio) phenylbis (4-fluorophenyl) sulfonium, 4- (phenylthio) phenylbis (4-methoxyphenyl) sulfonium, 4- (Phenylthio) phenyldi-p-tolylsulfonium, bis [4- (diphenylsulfonio) phenyl] sul
• X - is a counterion.
• the number of counterions is (p + 1) per molecule.
• counter ion is not particularly limited, for example, F -, Cl -, Br -, I - halogen ions such as; OH -; ClO 4 -; FSO 3 -, ClSO 3 -, CH 3 SO 3 -, C 6 H 5 SO 3 -, CF 3 SO 3 - sulfonate ion such as; HSO 4 -, sulfate ions of SO 4 2-like; HCO 3 -, CO 3 2- , carbonate ions and the like; H 2 PO 4-, HPO 4 2-, phosphate ions of PO 4 3- and the like; PF 6 -, PF 5 OH -, fluorophosphate ions such as fluorinated alkyl fluorophosphate ion; BF 4 -, B (C 6 F 5) 4 -, B (C 6 H 4 CF 3) 4 - -
• fluorinated alkylfluorophosphate ion examples include a fluorinated alkylfluorophosphate ion represented by the formula (C-1-3) and the like.
• R f represents an alkyl fluoride group.
• b is the number of R f and indicates an integer of 1 to 5.
• the b R fs may be the same or different from each other.
• B is preferably 2 to 4, more preferably 2 to 3.
• the alkyl fluoride group of R f represents a group in which a part or all of the hydrogen atom of the alkyl group is substituted with a fluorine atom.
• the number of carbon atoms of the alkyl group is preferably 1 to 8, and more preferably 1 to 4.
• Examples of the alkyl group include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group and octyl group; branched alkyl such as isopropyl group, isobutyl group, sec-butyl group and tert-butyl group.
• alkyl fluoride groups include CF 3- , CF 3 CF 2- , (CF 3 ) 2 CF-, CF 3 CF 2 CF 2- , CF 3 CF 2 CF 2 CF 2- , (CF 3 ). 2 CFCF 2- , CF 3 CF 2 (CF 3 ) CF-, (CF 3 ) 3 C- and the like can be mentioned.
• preferred fluorinated alkylfluorophosphate ions include [(CF 3 CF 2 ) 2 PF 4 ] - , [(CF 3 CF 2 ) 3 PF 3 ] - , [((CF 3 ) 2 CF) 2 PF 4 ] - , [((CF 3 ) 2 CF) 3 PF 3 ] - , [(CF 3 CF 2 CF 2 ) 2 PF 4 ] - , [(CF 3 CF 2 CF 2 ) 3 PF 3 ] - , [((CF 3 ) 2 CFCF 2 ) 2 PF 4 ] - , [((CF 3 ) 2 CFCF 2 ) 3 PF 3 ] - , [(CF 3 ) 2 CFCF 2 ) 3 PF 3 ] - , [(CF 3 CF 2 CF 2 ) 2 PF 4 ] - , [(CF 3 CF 2 CF 2 ) 3 PF 3 ] -
• diphenyl4-thiophenoxyphenylsulfonium tris (pentafluoroethyl) trifluorophosphate represented by the formula (C-2) and the formula (C-3) are represented.
• the triarylsulfonium salt hexafluoroantimonate can be particularly preferably used, and among these, the triarylsulfonium salt hexafluoroantimonate represented by the formula (C-3) is more preferable.
• the component (C) may be previously dissolved in a solvent in order to facilitate mixing with other components such as the component (A).
• the solvent is not particularly limited, and examples thereof include carbonates such as propylene carbonate, ethylene carbonate, 1,2-butylene carbonate, dimethyl carbonate, and diethyl carbonate.
• the content of the component (C) is preferably 0.1 part by mass or more with respect to 100 parts by mass in total of the components (A) and (B), and 0. More preferably, 15 parts by mass or more. Further, the content of the component (C) is preferably 5.0 parts by mass or less with respect to 100 parts by mass in total of the components (A) and (B) from the viewpoint of the adhesive durability of the cured product. More preferably, it is 0.0 parts by mass or less.
• the resin composition may further contain other components other than the component (A), the component (B) and the component (C).
• the curing retarder is a compound that suppresses an increase in viscosity after light irradiation and prolongs the pot life by temporarily capturing active species involved in the reaction.
• the curing retarder is preferably a curing retarder selected from the group consisting of a phosphoric acid-based curing retarder (component (D)) and an ether-based curing retarder (component (E)).
• the curing retarder may be used alone or in combination of two or more.
• the phosphoric acid-based curing retarder is a curing retarder selected from the group consisting of a phosphoric acid ester (component (D1)) and a phosphite ester (component (D2)).
• the component (D) may be used alone or in combination of two or more.
• the component (D1) may be used alone or in combination of two or more.
• the component (D1) is a compound represented by the formula (D1-1), a compound represented by the formula (D1-2), and a compound represented by the formula (D1-3) from the viewpoint of appropriate reactivity with cations and reduction of outgas. It is preferable to contain at least one selected from the group consisting of the compounds represented by, and it is more preferable to contain the compound represented by the formula (D1-2).
• R 2 in the formula (D1-2), R 3 and R 4, and, R 5 and R 6 in the formula (D1-3) is preferably in the formula of the same group.
• Examples of the substituent that the hydrocarbon group in R 1 , R 2 , R 3 , R 4 , R 5 and R 6 may have include an oxyalkyl group and the like.
• the hydrocarbon groups in R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are preferably unsubstituted hydrocarbon groups.
• the hydrocarbon group in R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is preferably an alkyl group or an aryl group, more preferably an alkyl group or a phenyl group, and is an alkyl group. Is even more preferable.
• the number of carbon atoms of the alkyl group may be, for example, 1 to 18, preferably 4 to 13.
• the compound represented by the formula (D1-1) may be, for example, monoalkyl phosphate (that is, a compound in which R 1 is an alkyl group), and specific examples thereof include monoethyl phosphate and mono n-butyl. Examples thereof include phosphate, mono (butoxyethyl) phosphate, mono (2-ethylhexyl) phosphate and the like.
• trialkyl phosphates i.e., compound R 2, R 3 and R 4 is an alkyl group
• the number of carbon atoms of the alkyl groups of R 2 , R 3 and R 4 is preferably 1 to 18, more preferably 4 to 12, and even more preferably 8.
• Examples of the compound represented by the formula (D1-3) include dialkyl phosphates (that is, compounds in which R 5 and R 6 are alkyl groups) and the like.
• Specific examples of the dialkyl phosphate include dibutyl phthalate and bis (2-ethylhexyl) phosphate.
• the (D2) component is a phosphite ester.
• Examples of the component (D2) include trimethylphosphite, triethylphosphite, trin-butylphosphite, tris (2-ethylhexyl) phosphite, triisooctylphosphite, tridecylphosphite, triisodecylphosphite, and the like.
• the component (D2) is represented by a compound represented by the formula (D2-1), a compound represented by the formula (D2-2), and a compound represented by the formula (D2-3) from the viewpoint of appropriate reactivity with a cation. It contains at least one selected from the group consisting of a compound, a compound represented by the formula (D2-4), a compound represented by the formula (D2-5) and a compound represented by the formula (D2-6). Is preferable.
• R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are independent of each other. Indicates a hydrocarbon group which may have a substituent.
• Substituents that the hydrocarbon groups in R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 may have include, for example, Examples thereof include an oxyalkyl group.
• the hydrocarbon groups in R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are preferably unsubstituted hydrocarbon groups.
• the hydrocarbon groups in R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are preferably alkyl or aryl groups. It is more preferably a group or a phenyl group, and even more preferably an alkyl group.
• the number of carbon atoms of the alkyl group may be, for example, 1 to 30, preferably 1 to 18.
• Examples of the compound represented by the formula (D2-1) include monoalkyl phosphite (that is, a compound in which R 7 is an alkyl group) and the like.
• Examples of the compound represented by the formula (D2-2) include dialkyl phosphite (that is, a compound in which R 8 and R 9 are alkyl groups) and the like.
• Examples of the compound represented by the formula (D2-3) include trialkylphosphite (that is, a compound in which R 10 , R 11 and R 12 are alkyl groups) and the like.
• Specific examples of the compound represented by the formula (D2-3) include triethyl phosphite, tris (2-ethylhexyl) phosphite, tridecyl phosphite, trilauryl phosphite, tris (tridecyl) phosphite, and trio.
• Examples include rail phosphite.
• Examples of the compound represented by the formula (C2-4) include bis (alkyl) pentaerythritol diphosphite (that is, a compound in which R 13 and R 14 are alkyl groups) and the like.
• Specific examples of the compound represented by the formula (D2-4) include bis (decyl) pentaerythritol diphosphite, bis (tridecylic) pentaerythritol diphosphite, and distearyl pentaerythritol diphosphite. ..
• Examples of the compound represented by the formula (D2-5) include dialkylhydrogen phosphite (that is, a compound in which R 15 and R 16 are alkyl groups) and the like.
• Specific examples of the compound represented by the formula (D2-5) include diethylhydrogen phosphite, bis (2-ethylhexyl) hydrogen phosphite, dilauryl hydrogen phosphite, diolayl hydrogen phosphite and the like.
• Examples of the compound represented by the formula (D2-6) include monoalkylhydrogen phosphite (that is, a compound in which R 17 is an alkyl group) and the like.
• Specific examples of the compound represented by the formula (D2-6) include monoethylhydrogen phosphite, mono (2-ethylhexyl) hydrogen phosphite, monolauryl hydrogen phosphite, monooleyl hydrogen phosphite and the like. ..
• the components (D2) include trimethylphosphite, triethylphosphite, tri-n-butylphosphite, tris (2-ethylhexyl) phosphite, triisooctylphosphite, tridecylphosphite, triisodecylphosphite, and tris (D2).
• Tridecyl) phosphite Tridecyl phosphite, trioleyl phosphite, tristearyl phosphite, triphenyl phosphite, tris (nonylphenyl) phosphite, diisodecylpentaerythritol diphosphite, bis (tridecyl) pentaerythritol diphosphite, distearyl pentaerythritol di Phosphite, bis (nonylphenyl) pentaerythritol diphosphite, dimethylhydrodienephosphite, dibutylhydrodienephosphite, di (2-ethylhexyl) hydrodienephosphite, dilaurylhydrodienephosphite, dioleylhydrodienphosphite It is preferable to contain at least one selected from the group consisting of
• Triisodecyl phosphite, tris (tridecyl) phosphite, trioleyl phosphite, tristearyl phosphite, triphenyl phosphite and tris (nonylphenyl) phosphite may contain at least one selected from the group. More preferable.
• the content of the component (D) is based on 100 parts by mass of the total of the components (A) and (B) from the viewpoint of obtaining a longer pot life. 0.01 parts by mass or more is preferable, and 0.02 parts by mass or more is more preferable.
• the content of the component (D) is preferably 2 parts by mass or less, preferably 1 part by mass, based on 100 parts by mass of the total of the components (A) and (B) from the viewpoint of moisture resistance and adhesive strength of the cured product. Less than a part is more preferable.
• the content of the component (D) is preferably 5 parts by mass or more from the viewpoint of obtaining a longer pot life with respect to 100 parts by mass of the component (C). More than 10 parts by mass is more preferable.
• the content of the component (D) is preferably 2000 parts by mass or less, more preferably 1000 parts by mass or less, with respect to 100 parts by mass of the component (C) from the viewpoint of photocurability.
• the component (E) is a curing retarder having an ether bond.
• the component (E) one type can be used alone or two or more types can be used in combination.
• the component (E) may be a chain ether or a cyclic ether.
• the chain ether include polyalkylene oxides such as polyethylene glycol, polypropylene glycol, and polyoxytetramethylene glycol.
• the cyclic ether include crown ether and the like.
• the component (E) is preferably a cyclic ether, more preferably a crown ether, from the viewpoint of appropriate reactivity with cations.
• the content of the component (E) is such that a longer pot life can be obtained with respect to a total of 100 parts by mass of the components (A) and (B). 0.1 part by mass or more is preferable, and 0.3 part by mass or more is more preferable.
• the content of the component (E) is preferably 5 parts by mass or less, preferably 3 parts by mass, based on 100 parts by mass of the total of the components (A) and (B) from the viewpoint of moisture resistance and adhesive strength of the cured product. Less than a part is more preferable.
• the content of the component (E) is preferably 5 parts by mass or more from the viewpoint of obtaining a longer pot life with respect to 100 parts by mass of the component (C). More than 10 parts by mass is more preferable.
• the content of the component (E) is preferably 2000 parts by mass or less, more preferably 1000 parts by mass or less, with respect to 100 parts by mass of the component (C) from the viewpoint of photocurability.
• the resin composition may further contain other components other than the component (A), the component (B), the component (C) and the component (X).
• Examples of other components include a photosensitizer.
• the photosensitizer is a compound that absorbs energy rays and efficiently generates cations from the photocationic polymerization initiator.
• the photosensitizer is not particularly limited, but benzophenone derivative, phenothiazine derivative, phenylketone derivative, naphthalene derivative, anthracene derivative, phenanthrene derivative, naphthacene derivative, chrysene derivative, perylene derivative, pentacene derivative, aclysine derivative, benzothiazole derivative, Benzoin derivative, fluorene derivative, naphthoquinone derivative, anthraquinone derivative, xanthene derivative, xantone derivative, thioxanthene derivative, thioxanthone derivative, coumarin derivative, ketocoumarin derivative, cyanine derivative, azine derivative, thiazine derivative, oxazine derivative, indolin derivative, azulene derivative, tri Examples thereof include allylmethane derivatives, phthalocyanine derivatives, spiropirane derivatives, spiroxazine derivatives, thiospiropiran
• At least one selected from the group consisting of anthracene derivatives such as 9,10-dibutoxyanthracene and phenylketone derivatives such as 2-hydroxy-2-methyl-1-phenyl-propane-1-one is preferable.
• 9,10-Dibutoxyanthracene and other anthracene derivatives are more preferred.
• the photosensitizer may be used alone or in combination of two or more.
• the content of the photosensitizer is preferably 0.01 part by mass or more, preferably 0.02 parts by mass or more, based on 100 parts by mass of the total of the components (A) and (B). More than parts by mass is more preferable.
• the content of the photosensitizer is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, based on 100 parts by mass of the total of the components (A) and (B). Within such a range, better curability and storage stability can be obtained.
• Examples of other components include silane coupling agents.
• the inclusion of the silane coupling agent tends to improve the adhesiveness and adhesive durability of the resin composition.
• the silane coupling agent is not particularly limited, but is ⁇ -chloropropyltrimethoxysilane, vinyltrimethoxysilane, vinyltricrolsilane, vinyltriethoxysilane, vinyl-tris ( ⁇ -methoxyethoxy) silane, ⁇ - (meth).
• ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane and ⁇ - (meth) acryloxipropyltrimethoxy At least one selected from the group consisting of silane is preferred.
• the silane coupling agent may be used alone or in combination of two or more.
• the content of the silane coupling agent is preferably 0.1 part by mass or more with respect to 100 parts by mass in total of the components (A) and (B). More than 2 parts by mass is more preferable.
• the content of the silane coupling agent is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, based on 100 parts by mass of the total of the components (A) and (B). With such a content range, higher adhesiveness and adhesive durability can be obtained.
• the method for producing the resin composition is not particularly limited, and for example, the above-mentioned components may be mixed.
• the mixing method is not particularly limited as long as each of the above-mentioned components can be sufficiently mixed.
• Examples of the mixing method include a stirring method using a stirring force accompanying the rotation of the propeller, a method using a normal disperser such as a planetary stirrer by rotation and revolution, and the like. These mixing methods are preferable in that stable mixing can be performed at low cost.
• the resin composition according to this embodiment may be used, for example, so as to contribute to the sealing of the organic EL display element.
• the resin composition may be used for forming a coating material for coating the organic EL display element, or may be used as an adhesive for adhering the members constituting the organic EL display device to each other.
• the viscosity of the resin composition according to this embodiment appropriately increases after light irradiation, and then cures as the polymerization reaction of the cationically polymerizable compound progresses.
• the resin composition after light irradiation can also be rapidly cured by heating.
• the light source for irradiating the resin composition is not particularly limited, and for example, a halogen lamp, a metal halide lamp, a high power metal halide lamp (containing indium, etc.), a low pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, and a xenon lamp. , Xenon excimer lamp, xenon flash lamp, light-emitting diode (hereinafter referred to as LED) and the like. These light sources are preferable in that they can efficiently irradiate energy rays corresponding to the reaction wavelength of the photocationic polymerization initiator.
• the above light sources have different radiation wavelengths and energy distributions. Therefore, the light source can be appropriately selected depending on the reaction wavelength of the photocationic polymerization initiator and the like. Natural light (sunlight) can also be a reaction initiation light source for the resin composition.
• irradiation method direct irradiation, focused irradiation with a reflecting mirror or the like, or focused irradiation with a fiber or the like may be performed. Irradiation using a low wavelength cut filter, a heat ray cut filter, a cold mirror, or the like can also be performed.
• the amount of light irradiation is not particularly limited, and may be appropriately adjusted depending on the thickness of the coating film of the resin composition and the like.
• the irradiation amount of light may be, for example, 50 to 20000 mJ / cm 2 , preferably 100 to 10000 mJ / cm 2 .
• the heating temperature is preferably 150 ° C. or lower, more preferably 80 ° C. or lower, from the viewpoint of avoiding damage to the organic EL display element.
• the heating temperature is preferably 50 ° C. or higher.
• the viscosity of the resin composition according to the present embodiment when measured using an E-type viscometer under the conditions of 25 ° C. and 10 rpm prevents unintentional dripping from a device used for ejection such as a dispenser or an inkjet device.
• a device used for ejection such as a dispenser or an inkjet device.
• 2 cps or more is preferable, and 5 cps or more is more preferable.
• the viscosity is preferably 200 cps or less, more preferably 50 cps or less, still more preferably 30 cps or less, from the viewpoint of ease of coating / discharging.
• the viscosity is 30 cps or less, ejection by an inkjet type device is easy at 25 ° C.
• the resin composition according to the present embodiment preferably has a viscosity 20 minutes after irradiation with light, which is 1.2 times or more and less than 10 times the viscosity before light irradiation.
• a viscosity 20 minutes after irradiation with light which is 1.2 times or more and less than 10 times the viscosity before light irradiation.
• 20 minutes after irradiating the resin composition coated so that the coating amount per unit area is 10 mg / cm 2 with ultraviolet rays at an irradiation amount of 100 mW / cm 2 for 10 seconds with a high-pressure mercury lamp.
• the viscosity is 1.2 times or more and less than 10 times the viscosity before ultraviolet irradiation.
• the resin composition according to the present embodiment preferably has a viscosity after curing for 10 minutes in a high temperature atmosphere after irradiation with light, which is 3 times or more the viscosity before curing.
• a viscosity after curing for 10 minutes in a high temperature atmosphere after irradiation with light which is 3 times or more the viscosity before curing.
• the viscosity 10 minutes after curing is preferably three times or more the viscosity before curing.
• the resin composition according to this embodiment can have a sufficiently long pot life after light irradiation. Further, since the viscosity of the resin composition according to the present embodiment appropriately increases after light irradiation, the members can be easily bonded and the workability is excellent. Further, the resin composition according to the present embodiment is excellent in moisture resistance and adhesiveness after curing. Therefore, according to the resin composition according to the present embodiment, a sealing material having excellent sealing characteristics can be formed, and an organic electroluminescence display device having excellent reliability can be manufactured.
• the encapsulant may contain a resin composition.
• the moisture permeability of at 0.1m thickness is preferably not more than 250g / (m 2 ⁇ 24hr) , is 200g / (m 2 ⁇ 24hr) or less Is more preferable.
• the moisture permeability of the cured product is based on JIS Z0208 "Moisture Permeability Test Method for Moisture-Proof Packaging Material (Cup Method)", using calcium chloride (anhydrous) as a moisture absorbent, and having an atmospheric temperature of 60 ° C. and relative humidity. The value measured under the condition of humidity 90% is shown.
• the cured product of the encapsulant according to the present embodiment has excellent transparency.
• the cured product has a total light transmittance of 60% or more, more preferably 80% or more, and 95% or more at a wavelength of 380 to 800 nm per 10 ⁇ m thickness. Is more preferable.
• the method of using the sealant according to the present embodiment is not particularly limited. For example, by applying a sealant to an object (for example, a member constituting an organic EL display device) and curing the sealant on the object, a sealant made of a cured body of the sealant is formed. it can.
• the sealing agent may be cured into a predetermined shape (for example, a film shape, a sheet shape, etc.) to form a sealing material having a predetermined shape.
• a predetermined shape for example, a film shape, a sheet shape, etc.
• the organic EL display element can be sealed by arranging the sealing material on the organic EL display element.
• the encapsulant may be made of a cured product of the encapsulant, or may contain a cured product of the encapsulant and other constituent materials.
• other constituent materials include an inorganic layer such as a silicon nitride film, a silicon oxide film, and silicon nitride, and an inorganic filler such as silica, mica, kaolin, talc, and aluminum oxide.
• an organic EL display device including an organic EL display element and a sealing material can be easily manufactured.
• the method for manufacturing the organic EL display device is, for example, an attachment step of attaching the above-mentioned sealing agent to the first member, an irradiation step of irradiating the attached sealing agent with light, and a light-irradiated sealing. It may include a bonding step of bonding the first member and the second member via an agent. According to such a manufacturing method, the joint surface between the first member and the second member constituting the organic EL display device can be sealed with a sealing material.
• the sealant placed on the first member in the adhesion process thickens by light irradiation.
• the first member and the second member are bonded to each other until the light-irradiated sealant is cured, so that the first member and the second member are bonded to each other. Is glued by.
• the sealant interposed between the first member and the second member is cured by post-heating, if necessary, to form a sealant.
• the process after the irradiation step may be carried out by blocking light.
• the second member can be adhered to the first member without being exposed to light.
• the method of attaching the sealant is not particularly limited, and may be, for example, an inkjet method, a method using a dispenser, or the like.
• the first member and the second member may be any members constituting the organic EL display device, and are not particularly limited.
• the first member may be an organic EL display element and the second member may be a substrate.
• the first member may be a substrate
• the second member may be an organic EL display element
• the type of substrate is not particularly limited, and examples thereof include a glass substrate, a silicon substrate, and a plastic substrate. Of these, a glass substrate and a plastic substrate are preferable, and a glass substrate is more preferable.
• Examples 1 to 13 and Comparative Examples 1 to 3 ⁇ Preparation of sealant>
• Each component shown in Table 1 was mixed at the composition ratio (part by mass) shown in Table 1 to prepare the encapsulant of the example.
• the viscosity of the sealant and the ejection property in an inkjet device were evaluated by the following evaluation methods.
• the obtained encapsulant was cured under the following photocuring conditions to form a cured product, and the moisture permeability, yellowness, transmittance and organic EL evaluation of the cured product were measured by the evaluation methods shown below. ..
• Each component shown in Table 1 means the following.
• Viscosity measurement method The viscosity was measured using an E-type viscometer (cone rotor: 1 ° 34'x R24, "DV3T” manufactured by BROOKFIELD) under the conditions of a temperature of 25 ° C. and a rotation speed of 10 rpm.
• An inkjet ejection device (MID500B manufactured by Musashi Engineering Co., Ltd., solvent-based head "MID head") is placed on a 70 mm ⁇ 70 mm ⁇ 0.7 mmt base material (non-alkali glass (Eagle XG manufactured by Corning Inc.)) of the obtained composition. Discharged using. Dischargeability was evaluated according to the following criteria. A: The nozzle can be discharged without clogging. B: The nozzle is clogged and cannot be discharged.
• the sealant was photocured under the conditions of a wavelength of 365 nm and an integrated light intensity of 1,000 mJ / cm 2 using a UV curing device (manufactured by Fusion) equipped with an electrodeless discharge metal halide lamp. Then, heat treatment was carried out for 30 minutes in an oven at 80 ° C. to prepare a cured product.
• [Humidity permeability] A sheet-shaped cured product having a thickness of 0.1 mm was produced under the above curing conditions. According to JIS Z0208 "Moisture Permeability Test Method for Moisture-Proof Packaging Material (Cup Method)", calcium chloride (anhydrous) is used as a moisture absorbent, and the moisture permeability of the cured product is measured under the conditions of an ambient temperature of 60 ° C. and a relative humidity of 90%. did. The moisture permeability is 250g / (m 2 ⁇ 24hr) or less.
• Anode ITO anode film thickness 250 nm ⁇ Hole injection layer Copper phthalocyanine Thickness 30 nm -Hole transport layer N, N'-diphenyl-N, N'-dinaphthylbenzidine ( ⁇ -NPD) 20 nm thick -Light emitting layer Tris (8-hydroxyquinolinato) aluminum (metal complex material), light emitting layer film thickness 1000 ⁇ ⁇ Electron injection layer Lithium fluoride Thickness 1 nm ⁇ Cathode aluminum, anode film thickness 250 nm
• the organic EL display element immediately after production is exposed for 1000 hours under the conditions of 60 ° C. and 90% by mass relative humidity, then a voltage of 6 V is applied for 10 seconds, and the light emitting state of the organic EL display element is visually and microscopically observed. It was observed and the diameter of the dark spot was measured.
• the diameter of the dark spot is preferably 300 ⁇ m or less, more preferably 50 ⁇ m or less, and further preferably no dark spot.
• Table 1 shows the results of each of the above evaluations. According to the encapsulant of the example, it was shown that the viscosity was low and the reliability after curing was excellent. Further, when the content of the component (A) is less than 50 parts by mass out of a total of 100 parts by mass of the components (A) and (B), the viscosity of the sealant becomes high and the coating / discharging property deteriorates. It was shown (Comparative Examples 1 and 2). Furthermore, it was shown that the encapsulant did not cure when the component (C) was not used (Comparative Example 3).
• the resin composition according to the present embodiment includes, for example, a sealing agent for an organic electroluminescence (EL) display element containing the resin composition, a sealing material for an organic EL display element containing a cured product of the sealing agent, and a sealing material for an organic EL display element.
• a sealing agent for an organic electroluminescence (EL) display element containing the resin composition for example, a sealing agent for an organic electroluminescence (EL) display element containing the resin composition
• a sealing material for an organic EL display element containing a cured product of the sealing agent a sealing material for an organic EL display element.

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• 2020
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